Dear David WygantHey,

Just as I’ve done for the guys, I’m starting a “Dear David” day on the blog where I’ll answer one of your questions and post it here. Don’t worry I won’t mention any names if you prefer, so if you have a burning dating question, or need some relationship advice drop me an email. It might be your “Dear David,” I feature next week.

Kicking things off is a question from Denise who has an issue with a guy in her local diner. Here’s the email she sent…


Dear David,                                        

There’s this guy I like. He’s a waiter in a local diner I frequent often. He smiles, I smile. He’ll seat me in his section, and he always comes back to my table to talk to me.

Recently he made it a big deal to tell me he is single.

He even calls me by my name. He seems sweet, kind, and sensitive. He seems the kind of man who’s been brought up right. He’s a gentleman. I’m quite a few years older than he is but by sight, no one would know. I’m lucky I look good for my age.  

But here’s my question…

If he’s interested in me, why hasn’t he asked me out yet?

We have great conversations. We laugh together. And he’s obviously flirting with me. So what should I do next?

I’m in there a few times a week, and always end up in his section. Should I ask him out myself, or wait for him to make a move?

I’m worried he’s just being friendly and I don’t want to make myself look stupid. Am I reading the signs wrong, or could he be interested?  



David says…

This is the problem with men nowadays.

They’re so chicken, it’s ridiculous.

They hesitate, they wait, and they debate. They don’t have the balls to ask a woman out.  It’s crazy, isn’t it?

In the good old days, a man would see a woman and claim her. He’d look at her and say, “I want to go out with you.”

No hesitation and no messing around.  

I don’t know about you, but this would really frustrate me if I were a woman. First off, who cares if you’re older and he’s younger. That doesn’t make a difference. Here’s what do you need to do. You need to be a little ballsy. I would just leave your phone number under the coffee cup with your tip, and say, “Let’s take this outside the restaurant.”

That is the only way to do it.

You may not feel comfortable going back if he doesn’t call you. But then again, you can find another local diner to go. If that approach doesn’t work for you, look at him and say, “We should really get to know each other a little better.”

Drop the hint.

It’s crazy how passive men are, and I feel for all you women.  Unfortunately, not every man is a David Wygant man that’s going to come over and ask you out right away. Women now have to be a little more aggressive when it comes to dating and making the first move. Best of luck!